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2-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-5-[1-pyridin-2-ylmethylidene]cyclopent-2-enone → Rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

HRID 514195
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 514195
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:10](=[O:23])[C:11](=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:4]([CH3:24])[CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([CH3:24])[C:5]([C:9]2[C:10](=[O:23])[CH:11]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH2:12][C:13]=2[O:14][CH3:15])=[C:6]([CH3:8])[CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 896012732-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-5-[1-pyridin-2-ylmethylidene]cyclopent-2-enone

Produkt 1

HCID 89600800Rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

To a solution of 2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-[1-pyridin-2-ylmethylidene]cyclopent-2-enone (2.8 g, 7.3 mmol) in acetic acid (30 ml) is added zinc powder (2.3 g, 36.5 mmol) at 25-30°C. The resulting suspension is stirred at 25-30°C. for 6-7 hours, then filtered through a bed of diatomaceous earth and washed with methanol (20 ml×2). The filtrate is concentrated under vacuum, water is added and the crude product is extracted with ethyl acetate (50 ml×3). The combined organic fractions are washed with distilled water, brine, dried over sodium sulfate, filtered and the filtrate concentrated in vacuo. The crude is purified by flash column chromatography to afford rac-2-(4-bromo-2,6-dimethylphenyl)-3-methoxy-5-pyridin-2-ylmethylcyclopent-2-enone.

Aufarbeitung

  1. filtrationfiltered through a bed of diatomaceous earth
  2. washwashed with methanol (20 ml×2)
  3. concentrationThe filtrate is concentrated under vacuum, water
  4. additionis added
  5. extractionthe crude product is extracted with ethyl acetate (50 ml×3)
  6. washThe combined organic fractions are washed with distilled water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo
  10. customThe crude is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-87e37a4ea38449e5bfaf055355f0f61e
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09107415B2

Notizen zur Reaktion

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